bookbear express

bookbear express

Friendship maintenance

how to make it all work

Ava's avatar
Ava
Dec 21, 2025
∙ Paid
Egon Schiele, Town among the Greenery (The Old City III), 1917

Hello! If you’re new here you can find the previous posts in this friendship series here:

  1. Radical fun - on the friendship theory of everything

  2. Prioritize your favorite people

  3. How do I meet more people I like?

  4. Is friendship romantic?

Sorry I’m late with my post this week :) I have been very horizontal with the flu, and am slowly regaining mobility.

I’m on my way back from New York after a three day trip to catch the premiere of a documentary series that T directed. I stayed at the Park Slope apartment of two other friends, who also went to the premiere. I spent Thanksgiving with friends, put together a gift guide with friends last week, and plan to spend New Year’s Eve with friends. It’s been a really satisfying year for friendship—I keep joking that I’ve been too busy hanging out with my friends to write about friendship, which is an entirely lovely problem to have.

Lately I’ve been reflecting on how a Friend Group is a large, tottering and unstable structure. Each of my friendships is constantly shifting. Friends get busy and less busy. Friends get into relationships and become more distant, friends get out of relationships and become more intimate. Friends get new jobs, quit their jobs, start companies, have crises, go on three-month trips to Japan, threaten to move to Europe. Fights and friction inevitably occur.

Over time, I’ve been trying to learn how to be more intentional and spontaneous in all of my friendships. Intentional as in: taking trips with friends, spending meaningful one-on-one time together, creating rituals and routines, picking up little gifts here and there, expressing love actively. Spontaneous as in: being accepting and relaxed with regard to the natural ebb and flow of friendship, and believing that the people who really love you will always come back.

Being loved by my friends has taught me that it’s okay for people to be where they are. When you feel that sense of acceptance, it’s possible to approach relationships with a sense of ease: to communicate honestly and earnestly without fear. I’ve noticed that I’m much more willing now to take social risks than I was a few years ago, because I feel much more confident in the love I already have. My friend C describes this as “knowing that he has a community that will always catch him.”

Security comes from knowing that you’re loved deeply and loved well. There’s no shortcut to being loved well other than time and maintenance. I’ve never felt as secure in my friendships as I do now, at age 29. I’m assuming that when I’m 58 I will have acquired the composure of a large tortoise. It takes a long time to really feel like you know someone. Year One of a friendship is so different from Year 5 or Year 10. Love over time is deep magic, and maintenance is what gets us there.

What does maintenance actually look like?

  1. It looks different for different friendships. No two people are the same, and no two friendships are the same. N and I text constantly, and hang out sporadically. L and I have intense and alive conversations in person, but don’t text that much. C and I share a specific sense of humor. I have friends I primarily see in groups and friends I only see one-on-one.

  2. On some level, it’s purely a time game. If you want a very deep and reliable friendship with someone, you have to spend a lot of time with them. This is easiest if they live close to you, but if you don’t you have to contrive ways to stay in contact. Get creative with it!

  3. It’s nice to have rituals. Always getting brunch at the same restaurant. Hosting a joint birthday party together every year.

  4. I’ve come around on location sharing. I used to find sharing my location with friends really weird. But I’ve since become a huge fan—I love seeing where everyone is! I use it often for practical purposes like estimating how late a friend will be to a restaurant or checking who is at what party, but it’s also really fun to open Find My and just be like, Huh, why is Brendan in Norway?

  5. Related: proximity makes things way easier. I really like how physically small of a city San Francisco is. I also really like living in the same neighborhood as a bunch of my friends. I frequently run into people I know at coffee shops or just walking around, and it makes things so easy. It’s so much easier to be close to friends when you organically bump into them all the time, which is why I feel no shame about my constant campaign to get everyone I love to move to California.

  6. You don’t have to reinvent the wheel constantly. T likes to say this about our phone calls: We can talk about the same topic 100 times over without saying anything new but we have just as much fun each time. Having a great relationship with someone doesn’t require constant novelty—it just means really enjoying the person’s thoughts, personality, and conversation.

  7. Conflict can bring friends closer. It doesn’t even have to be active conflict, like actually having a fight—sometimes closeness after a period of unaddressed alienation (like a friend dropping off the face of the earth for six months) can reaffirm the durability of the relationship. You both know you want to keep the relationship going, and that counts for a lot.

  8. Inconvenience really is the price of community. Going to parties when you’d rather stay in, taking a red-eye to make it to a friend’s birthday, having one too many drinks and compromising your Oura ring sleep score, fielding the 50th call from your friend complaining about your boyfriend… these are features, not bugs. It’s a privilege to not get to live life primarily on your own terms.

How do you get closer to someone?

Here’s what you guys told me in the friendship survey:

  • Repeated shared positive (and stressful-turned-positive) experiences that let our personalities shine and gel - late night studying in dorms, organizing hackathons and making them happen, shared interests in climbing, being able to spend 8 hours chatting and feeling energetic, climbing trips, work coffee runs / happy hours / ranting about our jobs

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